The road to employment begins in high school. However, few youth with severe disabilities currently participate in paid employment before graduation. The purpose of this study was to map the breadth of barriers that can hinder youth from accessing this influential transition experience. We held individual (n = 8) and focus group (n = 16) interviews with 74 transition stakeholders, including parents, educators, adult agency staff, school district leaders, and local employers. Collectively, they identified 47 barriers falling within eight broad categories of challenges: school, student, family, workplace, service system, partnership, transportation, and community. Although there were areas of clear consensus, noticeable differences were evident in the concerns raised by each of these five stakeholder groups. We present recommendations for research and practice aimed at connecting more youth with severe disabilities to early work experiences that can change their post-school employment trajectories.